US994841A - Explosive. - Google Patents
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- Publication number
- US994841A US994841A US56693410A US1910566934A US994841A US 994841 A US994841 A US 994841A US 56693410 A US56693410 A US 56693410A US 1910566934 A US1910566934 A US 1910566934A US 994841 A US994841 A US 994841A
- Authority
- US
- United States
- Prior art keywords
- butylene glycol
- nitro
- glycerin
- nitrate
- explosive
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002360 explosive Substances 0.000 title description 10
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 14
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical class [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 10
- 229960003711 glyceryl trinitrate Drugs 0.000 description 10
- 239000000006 Nitroglycerin Substances 0.000 description 9
- FBOGSWRRYABFKU-UHFFFAOYSA-N 4-hydroxybutyl nitrate Chemical compound OCCCCO[N+]([O-])=O FBOGSWRRYABFKU-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical class CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 229910002651 NO3 Inorganic materials 0.000 description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- 150000002823 nitrates Chemical class 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AIAZHSDLSLGTCS-UHFFFAOYSA-N 1-nitrobutane-1,4-diol Chemical compound OCCCC(O)[N+]([O-])=O AIAZHSDLSLGTCS-UHFFFAOYSA-N 0.000 description 2
- 229910000497 Amalgam Inorganic materials 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- -1 for instance Chemical compound 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 229920001220 nitrocellulos Polymers 0.000 description 2
- 229940079938 nitrocellulose Drugs 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- XSSPJUWPQUUOIK-UHFFFAOYSA-N 1,1-dinitrobutane-1,4-diol Chemical compound [N+](=O)([O-])C(CCCO)([N+](=O)[O-])O XSSPJUWPQUUOIK-UHFFFAOYSA-N 0.000 description 1
- QELUAJBXJAWSRC-UHFFFAOYSA-N 4-nitrooxybutyl nitrate Chemical compound [O-][N+](=O)OCCCCO[N+]([O-])=O QELUAJBXJAWSRC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 229910000761 Aluminium amalgam Inorganic materials 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/02—Preparation of esters of nitric acid
Definitions
- This nitro-glycerin has certain defects, among which it may be stated that the glycerin which is its base is expensive, and the temperature of explosion of the explosive mixture ofthe nitro-glycerin is very.
- the butylene glycol is represented 1n formula in the following manner:
- I produce the butylene glycol in the following manner: I take ethyl alcohol (C H OH) which may be de-natured without affecting the result. This ethyl alcohol is first oxidized. Preferably I accomplish this oxidation by the ordinar catalytic oxidation from the air, such for'lnstance, by using metallic platinum or copper and heat. The resultant is acct-aldehyde (C H O) This acetaldehyde is then condensed. I have used for this condensation an aqueous solution of an alkaline carbonate, for instance, potassium carbonate; 450 grams of acetalde- .hyde were cooled to --5 C. and 200 grams of powdered ice then added.
- C H OH ethyl alcohol
- This ethyl alcohol is first oxidized.
- I accomplish this oxidation by the ordinar catalytic oxidation from the air, such for'lnstance, by using metallic platinum or copper and heat.
- the condensation can be produced by other alkaline carbonate or a borate, phosphate, acetate or cyamd, of the alkaline metals or alkaline earths.
- the resultant of this condensation is acetaldol (0 11 0
- This condensation product is then reduced to butylene glycol by means of a reducing agent, and I have employed the following IHQiLhOClZ-Thfi aqueous solution of acetaldol', obtained by ctmdensing 450 grams of acetaldehyde with potassium carbonate was diluted to six literswit h ice- ,water, rendered neutral by the addition of hydrochloric acid and then 142 grams of aluminum amalgam added. After standmg for two days, the aluminum hydroxid I was filtered off and a further 58 grams of the amalgam added, and the mixture left for a further two days. After filtering the solution, the butylene glycol was recovered.
- butylene glycol exists in an aqueous solution and is isolated by simple distillation, preferably. under vacuum.
- This butylene glycol may then be nitrated in the same manner that lycerin is nitrated, by means of nitric acid and sulfuric acid in the following manner: 350 grams of ordinary nitratmg acld'such as is used for the nitration of glycerin were cooled to 5 'Ceancl then 50 grams of butylene glycol slowly introduced into this, under the surface of-the liquid in a fine spray, the acid mixture being kept at -5 C. and agitated vigorously throughout theaddition.
- the resultant nitrated compound may then be used by. itself or
- Butylenegly'col nitrate 1 partby weight; nitro-glycerin, 3 parts by weight.
- Butylene glycol nitrate 3 parts by weight; nitro-starch, 1 part by weight.
- Butylene glycol nitrate 1 part by weight
- nitro-butylene glycol I intend to include the mononitro-butylene glycol and the di-nitro-butylene glycohalthough I have only shown the formula of the di-nitro-butylene glycol.
- An explosive containing an admixture of" butylene glycol nitrate and a nitrate.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
UNITED STATES PATENT OFFICE.
HAROLD HIIBBERT, OF WILMINGTON, DELAWARE, ASSIGNOR TO E. I. DU PONT DE NEMOURS POWDER COMPANY, OF WILMINGTON, DELAWARE, A CORPORATION OF NEW JERSEY.
EXPLOSIVE.
N 0 Drawing.
Specification of Letters Patent. Patented June 13, 1911, Application filed June 15, 1910. Serial No. 566,934. I
This nitro-glycerin has certain defects, among which it may be stated that the glycerin which is its base is expensive, and the temperature of explosion of the explosive mixture ofthe nitro-glycerin is very.
high, which makes it in many cases not a good ingredient for smokeless powder.
I have discovered that if butylene glycol nitrate be formed, a product is obtained whose temperature of explosive ignition is lower than that of nitro-glycerin, which enables it to be freely used as an ingredient of smokeless powder, safety explosives and dynamite. 'Further, I have discovered that such compound may be combined with nitrates or nitro compounds,such, for instance, as examples of nitrates nitro-cellulose or nitro starch, toform a colloid of such mixtures. It also may be mixed with nitroglycerin, and the resulting mixture has a lower freezing point and is more stable than nitro-glycerin.
WVhile butylene glycol is known and is described in text books, I believe myself to.
be the first to have discovered nitratedbut-ylene glycol andits value for the purposes named. Further, the method of making butylene glycol, as set out in the text books, is so complicated as to render it very expensive and difiicult to carry out. My discovery, therefore, includes a simple method for directly producing this, butylene glycol as well as the nitrated butylene glycol.
The butylene glycol is represented 1n formula in the following manner:
ens-( 211011 onion and when nitrated the formula is thus represented CH -CHNO:
I produce the butylene glycol in the following manner: I take ethyl alcohol (C H OH) which may be de-natured without affecting the result. This ethyl alcohol is first oxidized. Preferably I accomplish this oxidation by the ordinar catalytic oxidation from the air, such for'lnstance, by using metallic platinum or copper and heat. The resultant is acct-aldehyde (C H O) This acetaldehyde is then condensed. I have used for this condensation an aqueous solution of an alkaline carbonate, for instance, potassium carbonate; 450 grams of acetalde- .hyde were cooled to --5 C. and 200 grams of powdered ice then added. A few drops of a cooled solution of potassium carbonate containing 19 grams of the carbonate in cubic centimeters of water were introduced into this mixture the temperature not being allowed to rise above +10 C. After standing some 10 or 15 minutes a further quan tity of the carbonate solution was intro. duced and again allowed to stand, contents being kept as nearlyas possible at a temperature of 0 C. After the whole of the carbonate had been added, the reactionproduct was kept in ice water for several hours to prevent any rise of temperature and then for a further 20 hours at +8 to +10 C. If the pure aoetaldol is required this may be extracted with ether, but for the purpose 'of'obtaining butylene gly'col this is unnecessary. -The condensation can be produced by other alkaline carbonate or a borate, phosphate, acetate or cyamd, of the alkaline metals or alkaline earths. The resultant of this condensation is acetaldol (0 11 0 This condensation product is then reduced to butylene glycol by means of a reducing agent, and I have employed the following IHQiLhOClZ-Thfi aqueous solution of acetaldol', obtained by ctmdensing 450 grams of acetaldehyde with potassium carbonate was diluted to six literswit h ice- ,water, rendered neutral by the addition of hydrochloric acid and then 142 grams of aluminum amalgam added. After standmg for two days, the aluminum hydroxid I was filtered off and a further 58 grams of the amalgam added, and the mixture left for a further two days. After filtering the solution, the butylene glycol was recovered.
by evaporating off the water. under reduced pressure. Other amalgams may be used and, further, the aluminum or other metal or an alloy or several metals may be used and also without the use of mercury. In this condition the butylene glycol exists in an aqueous solution and is isolated by simple distillation, preferably. under vacuum.
This butylene glycol may then be nitrated in the same manner that lycerin is nitrated, by means of nitric acid and sulfuric acid in the following manner: 350 grams of ordinary nitratmg acld'such as is used for the nitration of glycerin were cooled to 5 'Ceancl then 50 grams of butylene glycol slowly introduced into this, under the surface of-the liquid in a fine spray, the acid mixture being kept at -5 C. and agitated vigorously throughout theaddition.
The butylene glycol dinitrate at. once rises to the surface as a yellow oil and'mav be separated without further difiiculty from the acid mixture.
mixed with a nitrate or nitrates, as for'instance, nitroglycerln, IlltI'O-CQllll'lOSQS or nitro-starch. Indeed, I- have found it quite,
valuable when mixed with nitroglycerin as it"then lowers the: freezing point of nitroseparation after nitration a very simple 'mattcr. When mixed with nitro-glycerin it lowers the freezing point and promotes its stability. It colloids nitro-cellulose more effectively than .does nitro-glycerin and. such mixtures are very stable.
The resultant nitrated compound may then be used by. itself or The following are examples of admixtures containing butylene glycol nitrate:-
Butylenegly'col nitrate, 1 partby weight; nitro-glycerin, 3 parts by weight.
Butylene glycol nitrate, 3 parts by weight; nitro-starch, 1 part by weight.
' ;Butylene glycol nitrate, 1 part by'weight; intro-glycerin, 2 parts by weight; nitrostarch, 1 part by weight.
Butylene glycol nitrate, 1 part by weight;
glycerins, although I have shown only the formula of the tri-nitro-glycerin. In like manner, when- I use the term nitro-butylene glycol I intend to include the mononitro-butylene glycol and the di-nitro-butylene glycohalthough I have only shown the formula of the di-nitro-butylene glycol.
I do not herein claim the method of producing butylene glycol, as the same forms the subject matter of an application filed September 15, 1910, Serial No. 582,144, a division of this application. Nor do I claim herein specifically the explosive wherein a nitro derivative is used with nitrated butylene glycol, as this also is claimed in an application filed by me September 15, 1910, SerialNo. 582,145.
Having now fully described my invention, what I claim and desire to protect by Letters Patent 'is:
1. An explosive containing butylene glycol nitrate.
2. An explosive containing an admixture of" butylene glycol nitrate and a nitrate.
3. An explosive containing an admixture of butylene glycol nitrate and nitrates.
4:. An explosive containing an admixture of butylene glycol nitrate and nitro-glycerm. I v
In testimony of which inv'ention, I have hereunto set my hand, at Wilmington, on this 7th day of June, 1910.;
HAROLD HIBBERT.
copies of this pa ent may be obtained for five cents each, 'by addressing the Commissioner 0': Patents, Washington, .D. G.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56693410A US994841A (en) | 1910-06-15 | 1910-06-15 | Explosive. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56693410A US994841A (en) | 1910-06-15 | 1910-06-15 | Explosive. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US994841A true US994841A (en) | 1911-06-13 |
Family
ID=3063174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US56693410A Expired - Lifetime US994841A (en) | 1910-06-15 | 1910-06-15 | Explosive. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US994841A (en) |
-
1910
- 1910-06-15 US US56693410A patent/US994841A/en not_active Expired - Lifetime
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